Upon successive oxidative workup in a batch reactor, pyridine2,3dicarboxylic acid was obtained in 72. In this work, quinoline derivatives were synthesized from reaction of aniline, benzylaldehyde and dimethylacetylene dicarboxylate dmad in sequent steps to provide quinoline derivative dimethyl 2r, 3s, 4r2phenyl4phenylamino1, 3, 4trihydroquinoline2,3dicarboxylate 12. Tsa is a catalyst for both allyl ketone and quinoline synthetic steps. Quinoline not only has a wide range of biological and pharmacological activities but there are several established protocols for the synthesis of this ring. Pdf molecular docking and admet study of quinolinebased. The synthesis of indolo2,3bquinoline derivatives containing guanidine, amino acid or guanylamino acid substituents as well as their in vitro evaluation for the. Synthesis and antiproliferative activity of some quinoline. Synthesis of quinoline dicarboxylic esters as biocompatible. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. Organic chemistry quinoline quinoline derivative these keywords were added by machine and not by the authors. Novel quinoline derivatives carrying nitronesoximes nitric. Depending upon the location of the amino group, they can be divided into. Quinoline derivatives in general are known to have a variety of pharmacological and biological activities, such as immunodepresant activity 7, antimalarial activity 8 and antitubecular activity 9.
Synthesis of derivatives of 2 phenyl quinoline 4 carboxylic acid. Synthesis of new quinoline derivatives as antimicrobial agents. Synthesis of quinoline derivatives by multicomponent reaction. The derivative of the sum of two functions is the sums of their individual derivatives. Antiviral activity of novel quinoline derivatives against. Definition of derivative as we saw, as the change in x is made smaller and smaller, the value of the quotient often called the difference quotient comes closer and closer to 4. Isoquinoline isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring5. Quantum chemical investigations on quinoline derivatives.
Quinoline derivatives as possible lead compounds for antimalarial. The recent increase in development of chloroquineresistant strains of plasmodium falciparum and failure of vaccination program against malaria have fuelled the drug discovery program against this old and widespread disease. Antioxidant effect of quinoline derivatives containing or. In conclusion, several new quinoline 2one derivatives were synthesized via a new method for separating two isomers ii and iii by incorporation of a soxhlet apparatus, a novel experimental route was developed and used for isolation of a new compound iv which was prepared in good yield. Consideration of pyridine, pyrrole and quinoline derivatives evaluated by jecfa 63 rd meeting structurally related to pyridine, pyrrole, indole and quinoline derivatives evaluated by efsa in fge. Synthesis of substituted 4hydroxyalkylquinoline derivatives. It has a molecular formula of c 9 h 7 n and its molecular weight is 129. To produce derivative files, organizations use the archival master file or the production master file as a data source and produce one or more derivatives, each.
Quinoline itself has few applications, but many of its. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Quinoline is an alkaloid from various plant species including mentha species. Many quinolines recognized as antimalarial agents showed activity as antitb drugs. Quinoline derivatives, 6hydroxyquinoline, 6methoxyquinoline, 6bromoquinoline, 5nitroquinoline, 6nitroquinoline, 8aminoquinoline, mumbai, india. Quinoline definition of quinoline by the free dictionary. Indispensability of quinoline moiety in the field of. Pdf recent studies of antioxidant quinoline derivatives.
By controlling the regioselectivity of addition into our electrophilic intermediate, we also characterized by which mechanism the doebnermiller cyclization step occurred. Pdf biological activities of quinoline derivatives researchgate. Crystal structures of 3chloro2nitrobenzoic acid with. Quinoline is only slightly soluble in cold water but dissolvesreadily in hot water and most organic solvents. Aged samples, if exposed to light,become yellow and later brown. Molecular docking and admet study of quinolinebased derivatives for anticancer activity. Aminoquinolines are derivatives of quinoline, most notable for their roles as antimalarial drugs. Part of theorganic chemistry commons this dissertation is brought to you for free and open access by the iowa state university capstones, theses and dissertations at iowa state. The scope of the reaction was explored by using the catalytic system ru3co12nh4pf6. Quinoline is a heterocyclic aromatic organic compound with the chemical formula c9h7n. Quinoline 1 or 1azanapthalene or benzobpyridine is nitrogen containing heterocyclic aromatic compound. This process is experimental and the keywords may be. Introduction activity against pseudomonas vulgaris, staphylococcus aureus, aspergillus niger and pseudomonas chrysogenum. Synthesis of quinoline derivatives download pdf info.
Quinoline derivatives as possible lead compounds for anti. Molecular docking and admet study of quinoline based derivatives for anticancer activity. The effects of the temperature and substituents in the aromatic ring of the aniline were also evaluated. A new method to construct 4hydroxyalkylquinoline derivatives is described via cui and aui sequential catalyzed cyclization of anilines with aldehyde derivatives and aliphatic alkynes, respectively. Antimalarial drugs constitute a major part of antiprotozoal drugs and have been in practice for a long time. Safety and efficacy of pyridine and pyrrole derivatives. Friedlander prepared quinoline in 1882 by the condensation of o aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. May 29, 2018 this table shows the mic values of a few quinoline compounds that are active against grampositive bacterial strains including mrsa, mrse, vre and c. Multifunctional quinolinetriazole derivatives as potential modulators of amyloid.
Catalytic synthesis of tricyclic quinoline derivatives. Facilely accessible quinoline derivatives as potent antibacterial agents. In 1940s, synthetic quinoline compound chloroquine was introduced loeb et al. It has the formula c9h7n and is a colourless hygroscopic liquid with a strong odour. A new method to construct 4hydroxyalkyl quinoline derivatives is described via cui and aui sequential catalyzed cyclization of anilines with aldehyde derivatives and aliphatic alkynes, respectively. Several of quinoline quinolone derivatives displayed excellent. The synthesis of indolo2,3bquinoline derivatives containing guanidine, amino acid or guanylamino acid substituents as well as their in vitro evaluation for the cytotoxic and antifungal activity are reported.
It is a colorless hygroscopic liquid with a strong odor. Quinoline derivatives fused with various heterocycles india. The threecomponent cascade reaction provides an efficient approach for easy access to various new quinolinebased derivatives and quinoline containing an aliphatic chain substituent at the 4. Quinoline and its variety of derivatives have long been studied for their biological activities such as anticancer, antitumor, antiinflammatory, and antioxidant properties. Synthesis of quinoline derivatives by multicomponent. Scientific opinion on flavouring group evaluation 77, revision 1 fge. The lack of the selectivity of action of the indolo2,3b quinoline derivatives obtained so far prompted us to search further for more selective antitumor com. Pdf biological activities of quinoline derivatives.
Synthesis and biological activity investigation of some. Also present in cocoa, black tea and scotch whiskey. Synthesis and biological evaluation of quinoline derivatives. Quinolines have antiseptic, antipyretic, and antiperiodic properties and are used as antimalarials and for preparing other antimalarial drugs.
New quinoline2one derivatives were synthesized by reaction of 4,7dimethyl coumarin i with nitric acid in the presence of concentrated sulfuric acid to afford 4,7dimethyl6nitrocoumarin ii and 4,7dimethyl8nitrocoumarin iii. An external file that holds a picture, illustration, etc. Synthesis of imidazole derivatives bearing quinoline nucleus catalysed by can and their antimicrobial, antitubercular and molecular docking studies pratik g. The quinoline derivatives showed promising antiproliferative activity against hela human cervix cancer cell line and mdamb435 melanoma cell lines 6, 7, 14. Hexahydroquinoline derivatives have received considerable attention as leading pharmaceutical compounds due to their pivotal roles in various biological. Quinoline ring has been found to possess antimalarial, antibacterial, antifungal, anthelmintic, cardiotonic, anticonvulsant, antiinflammatory, and analgesic activity. Quinoline traditional synthesis are similar, departing from a simple aniline. Quinoline derivatives are prevalent in a variety of pharmacologically active synthetic and natural compounds. A brief history of quinoline as antimalarial agents. Pdf biological activities of quinoline derivatives suresh kumar. Catalytic synthesis of tricyclic quinoline derivatives from. A number of difficulttoobtain heterocyclic compounds tetrahydroquinolino and quinolinopyrazines were synthesized from odinitrotetrahydroquinolines. Pot synthesis of quinoline derivatives directly from. The aim of this work was to investigate the use of nbcl 5 as a lewis acid in multicomponent reactions between benzaldehyde, aniline derivatives and phenylacetylene in the synthesis of quinoline derivatives.
The uv spectra of the synthesized compounds were studied. Download pdf info publication number wo2000003991a1. The outline for the synthesis of polyfunctionalised dihydropyridine quinoline derivatives is presented graphically in scheme 1. Quinoline is a flavouring ingredient quinoline is a heterocyclic aromatic organic compound. Aged samples, especially if exposed to light, become yellow and later brown. The glycyl and lprolyl derivatives of 6hindolo quinoline 14 and 16 were obtained by reacting 9amino derivative 10 with the bocprotected amino acids using the 21hbenzo.
Guidance for the preparation of dossiers for sensory additives efsa feedap panel, 2012a, technical guidance for assessing the safety of feed additives. Among the pharmacologically important heterocyclic compounds, quinoline and its derivatives have been shown to possess antimalarial. The compound ii was treated with hydrazine hydrate 80% in pyridine to give n amino4,7dimethy 6nitroquinoline2one iv. Quinoline derivatives, 6hydroxyquinoline, 6methoxyquinoline. Keeping in view the activity of numerous quinoline derivatives reported as potential cognitive enhancers attempts were made to design and synthesize some 6aminoquinoline derivatives. Tmic is funded by genome alberta, genome british columbia, and genome canada, a notforprofit.
Synthesis of quinoline derivatives by a doebnervon miller reaction using a ag i exchanged montmorillonite k10 catalyst dissertation submitted to the university of kwazulunatal for the degree of master of science in chemistry by janeeka jayram school of chemistry and physics university of kwazulunatal january 2016. Pyridine derivatives structure and reactivity of oxypyridines, alkyl pyridines, pyridinium salts, and pyridine noxides. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Organometallic derivatives of quinoline and isoquinoline. Itis a colorless hygroscopic liquid with a strong odor. The 8 diethylaminohexylamino6methoxy4 quinoline and its derivatives have always. These agents have been designed by substituting quinoline scaffold with diverse chemical functionalities as well as by modifying quinoline quinolonebased antibacterial drugs. Preparation and antimicrobial activity evaluation of some quinoline. Synthesis of novel quinoline derivatives and their. Synthesis of quinoline derivatives by a doebnervon miller.
The parent compound 18 and new quinoline derivatives 1926 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using edcmediated peptide coupling reactions. The recent increase in development of chloroquineresistant strains of. Expired lifetime application number us239505a inventor francis d dodge original assignee. The biological potential of quinoline inspired us to explore further the quinoline derivatives. Grid files generation for protein is accomplished with receptor grid. Pdf quinoline derivatives constitute an important class of compounds for new drug development. The chloroquine 2 10 is the most famous drug containing this active ingredient resulted in control and treatment of malaria for decades 7. Synthesis and pharmacological evaluation of some quinoline. As part of our research, we are interested in the synthesis and development of heterocyclic compounds such as quinoline derivatives and polypyridyl materials that might have potential biological activities. Nov 09, 2012 quinoline is a heterocyclic aromatic organic compound with the chemical formula c9h7n. Facilely accessible quinoline derivatives as potent. This substance has been found in the following regulatory activities directly, or inheriting the regulatory context of a parent substance. Can functionalization of quinoline derivatives be exploited.
It can form salt with acids and displays reactions similar to those of pyridine. A few quinoline derivatives 42 developed by manera et al. Scheme 2 shows the eight compounds synthesized and used subsequently for further studies. Quinoline is a heterocyclic aromatic organic compound with the chemical formula c 9 h 7 n. Antioxidant effect of quinoline derivatives containing or not. Organometallic derivatives of quinoline and isoquinoline theodore stephen soddy iowa state college follow this and additional works at. Novel quinoline derivatives carrying nitrones and oxime as nitric oxide donors were synthesized. Eight novel polyfunctionalised dihydropyridine quinoline derivatives were synthesized, purified and characterized. Natural and synthetic quinoline derivatives as antituberculosis. The conversions of quinoline and 8nitroquinoline from singlepass experiments were 75.
Antimalarial agents generally belong to the class of quinoline which acts by interfering with heme metabolism. Quinoline and its derivatives represent a very important class of antimalarial drugs that function by parasite hemoglobin breakdown pathway. Structural modifications of quinolinebased antimalarial. The structure of some of the quinoline anticancer drug is shown in figure 1. The method allowed us to synthesize a wide range of quinoline derivatives and introduce different substituents by employing various simple starting materials. Quinoline derivatives, which widely occur in nature, especially alkaloids, have become an important skeleton in synthetic chemistry due to their variety of applications in medicinal, bioorganic, and industrial chemistry. Here you can find all of the regulations and regulatory lists in which this substance appears, according to the data available to echa.
Multifunctional quinolinetriazole derivatives as potential. As anticipated, electronreleasing substituents induce. Pdf quinoline and its fused heterocyclic derivatives tested with diverse pharmacological activity functional groups constitute an important. Considering the results obtained in vitro, a second objective of this study was to investigate the in vivo antinociceptive activity of compound with better antioxidant effect. Epa guidance documents that were used in the development of this. Ozonolysis of quinoline and quinoline derivatives in a. The threecomponent cascade reaction provides an efficient approach for easy access to various new quinoline based derivatives and quinoline.
This table shows the mic values of a few quinoline compounds that are active against grampositive bacterial strains including mrsa, mrse, vre and c. Preparation and antibacterial activity of some new 42heterylidenehydrazinyl7chloroquinoline derivatives. Manufacture process from the patents are flexible because more than one derivative can be produced from a similar reaction path. Quantum chemical investigations on quinoline derivatives as. Scientific opinion on flavouring group evaluation 77. Compound iv was then converted into a variety of derivatives.
Synthesis of new quinoline derivatives as antimicrobial. The title compounds were synthesized via an intermediate 6nitroquinoline which was prepared by skraup synthesis from 4nitroaniline prepared from. Novel quinoline derivatives carrying nitronesoximes. Quinoline derivatives are probably best known for their diverse pharmacological properties marella et al.
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